Guesthouse holiday rentals in Winter Park

Can't say enough about this charming house. Guests absolutely loved it! Definitely our go-to for the next show at Clarcona. Look forward to seeing you then.

If your visit to Orlando does not involve the parks, but the amazing Downtown Orlando, then this is the place for you. Hot water, comfy, cozy and homey.

Great little place in a cul-de-sac. Alvaro was incredibly friendly and helpful. I would gladly stay again.

The cabin is located behind the owner's house in a beautiful garden. We had use of a deck and seating on Lake Dora. It is a short and scenic drive along Lake Dora into the Mt. Dora. It is a scenic drive into Travares along the lake. In short, the cabin is ideally located and is a pleasant place to stay.

unbelievable tranquility hidden in the heart of Orlando

This was our second stay at Emily's cottage, and it did not disappoint. We returned to the Winter Park area to go kayaking on the nearby lakes and to enjoy the restaurants and museums. The cottage is centrally located on a quiet street. Definitely will stay again if we are in the area. Emily is an outstanding hostess.

Charming garden house, good hosts, excellent location, and the house itself has a nice feel. If you’re tall (6’2 or over), you may need to sleep slightly diagonally on the bed, which was fine. The AC is a somewhat older model but works. It has a really nice porch to sit outside and enjoy the lush vegetation.

I would definitely stay here again! Alex was a great host and the space is perfect!

Great place if you have a small family my kids enjoyed staying here as much as I did.

This was my second time staying here and it was still very good for the price. Mary is very nice and accommodating. I’ll be staying here everytime I visit Orlando.

Amazing hostess, quick with responses and super comprehensive and overall excellent service. House more beautiful in person and overall very homey and beautiful.

Amazing place, wonderful people, and the perfect location! Our whole stay was truly magical ✨. Everything was set up so thoughtfully , it felt like a home away from home. We loved every moment here, especially the bike rides around the beautiful area 🚲. The hosts have really created a space filled with warmth, comfort, and good energy ❤️. I highly recommend this place to anyone visiting Orlando, Florida — it’s a memory you’ll cherish forever! ✨🏡

I felt very comfortable staying here! It was a clean and beautiful space. I would definitely stay here again :)

A cozy, laid-back place. Will definitely stay again.

Ben was a great host and very attentive. His house is so lovely and I cant wait to book again!

What a beautiful place to be. If you do decide to stay. You’ll need more than a day. So make your trip count and get I for 2 days or more if possible. It has everything you need and will want. Within the property and what’s around it! God bless!

Located in Thornton Park, my favorite neighborhood in Orlando due to its walkability and quiet surroundings, Jeff’s place was just as described with all the comforts of home. Really enjoyed it and hope it’s available next time we make a road trip to Orlando!

Miriam and her husband were wonderful, friendly hosts. We loved the cottage which had everything we needed. The location is so peaceful and beautiful. Easy drive to Mt Dora and Lake Eustis. The pool was great. We have stayed in many Airbnbs and this was one of the best. Highly recommended.

We had long days in Orlando and Nicole’s place was a welcoming sanctuary for a cozy and warm space. And, the bed mattress was luxurious for a very comfortable night of rest.

Had a great stay, communication was great. We had a small hiccup with the hot tub and problem was solved very quickly. The only thing I would complain about and not really complaining is there were cloths and a used towel hanging on the back of the bathroom door. No biggie and honest mistake by cleaners other then that the stay was amazing and felt like home away from home. Will stay again for sure

Lovely place. Small cottage behind the main house, you have to walk behind the house to get to it. Large backyard (not completely fenced in). Perfect for my dog and I! 🐶

Had a wonderful and peaceful stay. Great neighborhood. Safe, quiet, and beautiful. Plenty of space and super comfy bed! Nadeem is very friendly and makes sure your stay has everything you need! Will stay again.

Great location, close to Disney and shopping. Quiet neighborhood. Check in/out was super easy. Magnolia was very accommodating.

Great place, I would only recommend to have some basic stuff , like oil and seasonings. Otherwise cute spot